1-甲基吲哚-2-胺盐酸盐 | 42456-82-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 1-甲基吲哚-2-胺盐酸盐
• 中文别名: 1-甲基-1H-吲哚-2-胺盐酸盐
• 英文名称: 2-amino-1-methylindole hydrochloride
• 英文别名: 1-Methyl-1H-indol-2-amine hydrochloride；1-methylindol-2-amine;hydrochloride
• CAS: 42456-82-6
• 化学式: C₉H₁₀N₂*ClH
• 分子量: 182.653
• InChiKey: DDIUVWLAXSJQBP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.18
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  31
• 氢给体数：
  2
• 氢受体数：
  1

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  1-甲基吲哚-2-胺盐酸盐 以98%的产率得到
  参考文献：
  名称：

  SAGITULLIN R. S.; KOST A. N.; MELNIKOVA T. V.; SHARBATYAN P. A., XIMIYA GETEROTSIKL. SOEDIN., 1977, HO 7, 945-951

  摘要：

  DOI：

文献信息

• Regiospecific Syntheses of 3-Aza-α-carbolines via Inverse Electron-Demand Diels-Alder Reactions of 2-Aminoindoles with 1,3,5-Triazines
  作者：Qun Dang、Xu Bai、Guoxing Xu、Lianyou Zheng、Shixue Wang

  DOI：10.1055/s-0029-1218345

  日期：2009.12

  scope of 1,3,5-triazine inverse electron-demand Diels-Alder (IDA) reactions was expanded to include 2-aminoindoles as productive dienophiles leading to various 3-aza-α-carbolines in excellent yields. Furthermore, the two ester groups of the IDA product were differentiated via reduction of the C4-ester to its corresponding alcohol. This new IDA reaction could be potentially applied to the synthesis of

  1,3,5-三嗪逆电子需求 Diels-Alder (IDA) 反应的范围扩大到包括 2-氨基吲哚作为生产亲二烯体，从而以优异的产率获得各种 3-氮杂-α-咔啉。此外，IDA 产品的两个酯基团是通过将 C4-酯还原为其相应的醇来区分的。这种新的 IDA 反应可用于合成各种可能具有神经保护活性的 3-氮杂-mescengrincin 类似物。
• Synthesis and antimicrobial activity of 2-amino-2-arylazoindole hydrochlorides
  作者：Yu. N. Portnov、V. G. Zabrodnyaya、S. N. Bulaga、L. N. Filitis、O. Yu. Amel'kin、V. A. Silin、O. V. Baklanova、E. N. Padeiskaya

  DOI：10.1007/bf00768381

  日期：1990.11

  aryldiazonium salts. Electrophiiic substitution reactions among the 2-aminoindoles (bromination, nitration, and sulfonation) yield substitution products in position 3 [3]. Substitution occurs at position 5 of the benzene ring only in strongly acid media where 2aminoindole exists in the iminoindole tautomer form [3]. Under the reaction conditions we selected (acetate buffer solution pH 5.0), the reaction between

  我们通过使 2-氨基-1-甲基吲哚 (I) 与芳基重氮盐反应合成了 2-氨基-3-芳基偶氮吲哚。2-氨基吲哚之间的亲电取代反应（溴化、硝化和磺化）在 3 位产生取代产物 [3]。仅在强酸性介质中苯环的 5 位发生取代，其中 2 氨基吲哚以亚氨基吲哚互变异构体形式存在 [3]。在我们选择的反应条件下（醋酸盐缓冲溶液 pH 5.0），重氮盐和 2-氨基-l-甲基吲哚 I 之间的反应更容易发生在位置 3，这更容易受到亲电攻击，导致形成2-氨基-3-芳基偶氮吲哚IIIa-m。
• ——
  作者：A. V. Sadovoy、G. A. Golubeva、O. E. Nasakin

  DOI：10.1023/a:1013292019317

  日期：——
• FeCl3-catalyzed sequential cyclization for the construction of 12-aryl 5,7-dihydropyrido[2,3-b:6,5-b']diindoles
  作者：Xiaoqian Chen、Lin Li、Changfeng Wan、Jin-Biao Liu

  DOI：10.1016/j.tetlet.2020.152334

  日期：2020.9

  A facile approach to prepare 12-aryl 5,7-dihydropyrido[2,3-b:6,5-b']diindoles via tandem cyclizations is described. FeCl3 is used as the catalyst for the reaction between o-aminophenylacetonitriles and aromatic aldehydes, generating 5,7-dihydropyrido[2,3-b:6,5-b']diindoles derivatives in moderate to high yields. (C) 2020 Elsevier Ltd. All rights reserved.
• Synthesis of novel galeterone derivatives and evaluation of their in vitro activity against prostate cancer cell lines
  作者：Radek Jorda、Eva Řezníčková、Urszula Kiełczewska、Jadwiga Maj、Jacek W. Morzycki、Leszek Siergiejczyk、Václav Bazgier、Karel Berka、Lucie Rárová、Agnieszka Wojtkielewicz

  DOI：10.1016/j.ejmech.2019.06.040

  日期：2019.10

  Prostate cancer is one of the main causes of male cancer-related deaths worldwide and the suppression of androgen receptor signalling is established as an effective strategy for the treatment. A series of galeterone analogues including several steroid-fused azacycles, as well as 17-(benzimidazol-1-ylimino), 16 alpha-(benzimidazol-2-ylamino), and 16 alpha-(benzothiazol-2-ylamino) steroid derivatives, were synthesized and tested against prostate cancer cell lines. Candidate compound 3f was shown to reduce AR-regulated transcription in a dose-dependent manner in nanomolar ranges and suppress expression of AR-regulated proteins Nkx3.1 and PSA in 22Rv1-ARE14 and VCaP cancer cell lines. Flexible docking study revealed similar position of 3f within AR binding site in comparison of galeterone even with stronger binding energy. (C) 2019 Elsevier Masson SAS. All rights reserved.